Design of oxa-spirocyclic PHOX ligands for the asymmetric synthesis of lorcaserin <i>via</i> iridium-catalyzed asymmetric hydrogenation
Xiang-Yu Ye, Zhiqin Liang, Cong Jin, Qiwei Lang, Gen‐Qiang Chen, Xumu Zhang
Abstract
in the presence of sodium tetrakis-3,5-bis(trifluoromethyl)phenylborate (NaBArF). The cationic iridium complexes showed high reactivity and excellent enantioselectivity in the asymmetric hydrogenation of 1-methylene-tetrahydro-benzo[d]azepin-2-ones (up to 99% yield and up to 99% ee). A key intermediate of the anti-obesity drug lorcaserin could be efficiently synthesized using this protocol.
Topics & Concepts
IridiumAsymmetric hydrogenationCatalysisChemistryCombinatorial chemistryEnantioselective synthesisStereochemistryOrganic chemistryAsymmetric Hydrogenation and CatalysisCyclopropane Reaction MechanismsAsymmetric Synthesis and Catalysis